CN107848989A - 新杂环化合物和包含其的有机发光器件 - Google Patents
新杂环化合物和包含其的有机发光器件 Download PDFInfo
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- CN107848989A CN107848989A CN201780002439.XA CN201780002439A CN107848989A CN 107848989 A CN107848989 A CN 107848989A CN 201780002439 A CN201780002439 A CN 201780002439A CN 107848989 A CN107848989 A CN 107848989A
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
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- 239000001257 hydrogen Substances 0.000 claims description 7
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
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- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 3
- 125000003368 amide group Chemical group 0.000 claims description 3
- 229910052805 deuterium Inorganic materials 0.000 claims description 3
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- YEYHFKBVNARCNE-UHFFFAOYSA-N pyrido[2,3-b]pyrazine Chemical compound N1=CC=NC2=CC=CN=C21 YEYHFKBVNARCNE-UHFFFAOYSA-N 0.000 description 1
- BWESROVQGZSBRX-UHFFFAOYSA-N pyrido[3,2-d]pyrimidine Chemical compound C1=NC=NC2=CC=CN=C21 BWESROVQGZSBRX-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- GNHGQOQUCKGFCV-UHFFFAOYSA-N quinolin-8-ol;zinc Chemical compound [Zn].C1=CN=C2C(O)=CC=CC2=C1 GNHGQOQUCKGFCV-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
- KZUNJOHGWZRPMI-UHFFFAOYSA-N samarium atom Chemical compound [Sm] KZUNJOHGWZRPMI-UHFFFAOYSA-N 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical compound C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- AGGKEGLBGGJEBZ-UHFFFAOYSA-N tetramethylenedisulfotetramine Chemical compound C1N(S2(=O)=O)CN3S(=O)(=O)N1CN2C3 AGGKEGLBGGJEBZ-UHFFFAOYSA-N 0.000 description 1
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- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical class C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- NAWDYIZEMPQZHO-UHFFFAOYSA-N ytterbium Chemical compound [Yb] NAWDYIZEMPQZHO-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
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- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
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- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
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- C07D277/62—Benzothiazoles
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- C07D333/76—Dibenzothiophenes
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Abstract
本公开提供了新的杂环化合物和包含其的有机发光器件。
Description
技术领域
相关申请的交叉引用
本申请要求于2016年7月20日向韩国知识产权局提交的韩国专利申请第10-2016-0092206号的权益,其公开内容通过引用整体并入本文。
本公开内容涉及新的杂环化合物和包含其的有机发光器件。
背景技术
通常,有机发光现象是指通过使用有机材料将电能转换成光能的现象。利用有机发光现象的有机发光器件具有这样的特性,例如视角宽,对比度优异,响应时间快,亮度、驱动电压和响应速度优异,因此已进行了许多研究。
有机发光器件通常具有这样的结构,其包括阳极、阴极以及设置在阳极与阴极之间的有机材料层。有机材料层常常具有包含不同材料的多层结构以提高有机发光器件的效率和稳定性,例如,有机材料层可由空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等构成。在有机发光器件的结构中,如果在两个电极之间施加电压,则空穴从阳极注入有机材料层并且电子从阴极注入有机材料层,当注入的空穴和电子彼此相遇时形成激子,并且当激子再返回基态时发光。
持续需要开发用于在这样的有机发光器件中所使用的有机材料的新材料。
现有技术文献
专利文献
(专利文献0001)韩国专利公开第10-2000-0051826号。
发明内容
技术问题
本公开内容涉及新的杂环化合物和包含其的有机发光器件。
技术方案
本公开内容提供了由以下化学式1表示的化合物。
[化学式1]
在化学式1中,
L1和L2各自独立地为单键;经取代或未经取代的C6-60亚芳基;或者经取代或未经取代的包含O、N、Si和S中至少一者的C2-60亚杂芳基,
Ar1为包含选自N、O和S中的1至3个杂原子的C2-60杂芳基,
Ar2为选自以下结构式中的任一者,
X为N(R'1)、C(R'2)(R'3)、Si(R'4)(R'5)、S或O,以及
R'1至R'7和R1至R19各自独立地为氢;氘;卤素;氰基;硝基;胺基;经取代或未经取代的C1-60烷基;C1-60卤代烷基;C1-60卤代烷氧基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含O、N、Si和S中至少一者的C2-60杂环基。
另外,本公开内容提供了有机发光器件,其包括:第一电极;设置成面向所述第一电极的第二电极;以及设置在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中所述有机材料层的一个或更多个层包含由化学式1表示的化合物。
有益效果
由化学式1表示的化合物可以用作有机发光器件的有机材料层的材料并且可以改善有机发光器件的效率、低驱动电压和/或寿命。特别地,由化学式1表示的化合物可用作用于空穴注入、空穴传输、空穴注入和传输、发光、电子传输、或电子注入的材料。
附图说明
图1示出了包括基底(1)、阳极(2)、发光层(3)和阴极(4)的有机发光器件的实例。
图2示出了包括基底(1)、阳极(2)、空穴注入层(5)、空穴传输层(6)、发光层(7)和阴极(4)的有机发光器件的实例。
具体实施方式
下文中,将更详细地描述本公开内容以帮助理解本发明。
本公开内容提供了由化学式1表示的化合物。
在本公开内容中,意指与另一取代基连接的单键。
如本文中使用的,术语“经取代或未经取代的”意指取代有选自以下的一个或更多个取代基:氘;卤素基团;腈基;硝基;羟基;羰基;酯基;酰亚胺基;胺基;氧化膦基团;烷氧基;芳氧基;烷基硫基;芳基硫基;烷基磺酰基;芳基磺酰基;甲硅烷基;硼基;烷基;环烷基;烯基;芳基;芳烷基;芳烯基;烷基芳基;烷基胺基;芳烷基胺基;杂芳基胺基;芳基胺基;芳基膦基;或包含N、O和S原子中至少一者的杂环基或未被取代,或者取代有所例示的取代基中的两个或更多个取代基连接的取代基或未被取代。例如,术语“两个或更多个取代基连接的取代基”可为联苯基。也就是说,联苯基可为芳基,或者可解释为两个苯基连接的取代基。
在本公开内容中,羰基的碳原子数没有特别限制,但优选为1至40。具体地,羰基可以为由以下结构表示的化合物,但不限于此。
在本公开内容中,酯基的氧可被具有1至25个碳原子的线性链、支化链或环状烷基,或者被具有6至25个碳原子的芳基取代。具体地,酯基可以为由以下结构表示的化合物,但不限于此。
在本公开内容中,酰亚胺基中的碳原子数没有特别限制,但优选为1至25。具体地,酰亚胺基可以为由以下结构表示的化合物,但不限于此。
在本公开内容中,甲硅烷基具体包括三甲基甲硅烷基、三乙基甲硅烷基、叔丁基二甲基甲硅烷基、乙烯基二甲基甲硅烷基、丙基二甲基甲硅烷基、三苯基甲硅烷基、二苯基甲硅烷基、苯基甲硅烷基等,但不限于此。
在本公开内容中,硼基具体包括三甲基硼基、三乙基硼基、叔丁基二甲基硼基、三苯基硼基、苯基硼基等,但不限于此。
在本公开内容中,卤素基团的实例包括氟、氯、溴或碘。
在本公开内容中,烷基可为线性链或支化链,并且其碳原子数没有特别限制,但优选为1至40。根据一个实施方案,烷基具有1至20个碳原子。根据另一个实施方案,烷基具有1至10个碳原子。根据另一个实施方案,烷基具有1至6个碳原子。烷基的具体实例包括甲基、乙基、丙基、正丙基、异丙基、丁基、正丁基、异丁基、叔丁基、仲丁基、1-甲基-丁基、1-乙基-丁基、戊基、正戊基、异戊基、新戊基、叔戊基、己基、正己基、1-甲基戊基、2-甲基戊基、4-甲基-2-戊基、3,3-二甲基丁基、2-乙基丁基、庚基、正庚基、1-甲基己基、环戊基甲基、环己基甲基、辛基、正辛基、叔辛基、1-甲基庚基、2-乙基己基、2-丙基戊基、正壬基、2,2-二甲基庚基、1-乙基-丙基、1,1-二甲基-丙基、异己基、2-甲基戊基、4-甲基己基、5-甲基己基等,但不限于此。
在本公开内容中,烯基可为线性链或支化链,并且其碳原子数没有特别限制,但优选为2至40。根据一个实施方案,烯基具有2至20个碳原子。根据另一个实施方案,烯基具有2至10个碳原子。根据另一个实施方案,烯基具有2至6个碳原子。其具体实例包括乙烯基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、3-戊烯基、3-甲基-1-丁烯基、1,3-丁二烯基、烯丙基、1-苯基乙烯基-1-基、2-苯基乙烯基-1-基、2,2-二苯基乙烯基-1-基、2-苯基-2-(萘基-1-基)乙烯基-1-基、2,2-双(二苯基-1-基)乙烯基-1-基、茋基、苯乙烯基等,但不限于此。
在本公开内容中,环烷基没有特别限制,但其碳原子数优选为3至60。根据一个实施方案,环烷基具有3至30个碳原子。根据另一个实施方案,环烷基具有3至20个碳原子。根据另一个实施方案,环烷基具有3至6个碳原子。其具体实例包括环丙基、环丁基、环戊基、3-甲基环戊基、2,3-二甲基环戊基、环己基、3-甲基环己基、4-甲基环己基、2,3-二甲基环己基、3,4,5-三甲基环己基、4-叔丁基环己基、环庚基、环辛基等,但不限于此。
在本公开内容中,芳基没有特别限制,但优选具有6至60个碳原子,并且可为单环芳基或多环芳基。根据一个实施方案,芳基具有6至30个碳原子。根据一个实施方案,芳基具有6至20个碳原子。作为单环芳基,芳基可为苯基、联苯基、三联苯基等,但不限于此。多环芳基的实例包括萘基、蒽基、菲基、芘基、苝基、基和芴基等,但不限于此。
在本公开内容中,芴基可以被取代,并且两个取代基可彼此键合形成螺环结构。在芴基被取代的情况下,可以形成
等。然而,并不限于此。
在本公开内容中,杂环基为包含O、N、Si和S中至少一者作为杂原子的杂环基,其碳原子数没有特别限制,但优选为2至60。杂环基的实例包括噻吩基、呋喃基、吡咯基、咪唑基、噻唑基、唑基、二唑基、三唑基、吡啶基、联吡啶基、嘧啶基、三嗪基、三唑基、吖啶基、哒嗪基、吡嗪基、喹啉基、喹唑啉基、喹喔啉基、酞嗪基、吡啶并嘧啶基、吡啶并吡嗪基、吡嗪并吡嗪基、异喹啉基、吲哚基、咔唑基、苯并唑基、苯并咪唑基、苯并噻唑基、苯并咔唑基、苯并噻吩基、二苯并噻吩基、苯并呋喃基、菲咯啉基、噻唑基、异唑基、二唑基、噻二唑基、苯并噻唑基、吩噻嗪基、二苯并呋喃基等,但不限于此。
在本公开内容中,芳烷基、芳烯基、烷基芳基和芳基胺基中的芳基与与上述芳基的实例相同。在本公开内容中,芳烷基、烷基芳基和烷基胺基中的烷基与上述烷基的实例相同。在本公开内容中,杂芳基胺基中的杂芳基可以应用上述对杂环基的描述。在本公开内容中,芳烯基中的烯基与上述烯基的实例相同。在本公开内容中,可以应用上述对芳基的描述,不同之处在于亚芳基是二价基团。在本公开内容中,可以应用上述对杂环基的描述,不同之处在于亚杂芳基是二价基团。在本公开内容中,可以应用上述对芳基或环烷基的描述,不同之处在于烃环不是一价基团而是通过结合两个取代基形成的。在本公开内容中,可以应用上述对杂环基的描述,不同之处在于杂环不是一价基团而是通过结合两个取代基形成的。
优选地,L1为单键或选自以下结构式中的任一者:
更优选地,L1为单键或选自以下结构式中的任一者:
优选地,L2为单键、更优选地,L2为单键、
优选地,Ar1为选自以下结构式中的任一者:
Y1至Y3中的两者为N,另一者为CH,
Z为N(Ar7)、S或O,以及
Ar3至Ar7为经取代或未经取代的C6-60芳基。
优选地,Ar3至Ar7为苯基或联苯基。
更优选地,Ar1为选自以下结构式中的任一者:
优选地,X为N-(苯基)、S或O。
优选地,R1为氰基、三氟甲基或三氟甲氧基。
优选地,R2至R19为氢。
由化学式1表示的化合物可以选自以下化合物:
由化学式1表示的化合物可以如以以下反应式1进行制备:
[反应式1]
可通过使由化学式1-a表示的化合物与由化学式1-b表示的化合物反应,或者通过使由化学式1-c表示的化合物与由化学式1-d表示的化合物反应来进行反应以制备由化学式1表示的化合物。该反应为Suzuki偶联反应,优选在钯催化剂和碱的存在下进行。用于Suzuki偶联反应的官能团可以如本领域已知的那样进行改变。上述制备方法可在后面描述的制备例中进一步详细说明。
另外,本公开内容提供了包含由化学式1表示的化合物的有机发光器件。在一个实例中,本公开内容提供了有机发光器件,其包括:第一电极;设置成面向所述第一电极的第二电极;以及设置在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中所述有机材料层的一个或更多个层包含化学式1的化合物。
本公开内容的有机发光器件的有机材料层可具有单层结构或者其中层合有两个或更多个有机材料层的多层结构。例如,本公开内容的有机发光器件可具有这样的结构,其包括空穴注入层、空穴传输层、发光层、电子传输层、电子注入层等作为有机材料层。然而,有机发光器件的结构不限于此,而是可以包括更少数量的有机层。
此外,有机材料层可以包括空穴注入层、空穴传输层或者同时注入和传输空穴的层,并且空穴注入层、空穴传输层或者同时注入和传输空穴的层包含由化学式1表示的化合物。
此外,有机材料层可以包括发光层,并且发光层包含由化学式1表示的化合物。
此外,有机材料层可以包括电子传输层或电子注入层,并且电子传输层或电子注入层包含由化学式1表示的化合物。
此外,电子传输层、电子注入层或者同事传输和注入电子的层包含由化学式1表示的化合物。
此外,有机材料层包括发光层和电子传输层,并且电子传输层可以包含由化学式1表示的化合物。
此外,根据本公开内容的有机发光器件可以为具有其中阳极、一个或更多个有机材料层和阴极依次层合在基底上的结构(正常型)的有机发光器件。此外,根据本公开内容的有机发光器件可以为具有其中阴极、一个或更多个有机材料层和阳极依次层合在基底上的反向结构(倒置型)的有机发光器件。例如,根据本公开内容的有机发光器件的结构示于图1和图2中。
图1示出了包括基底(1)、阳极(2)、发光层(3)和阴极(4)的有机发光器件的实例。在这样的结构中,由化学式1表示的化合物可包含在发光层中。
图2示出了包括基底(1)、阳极(2)、空穴注入层(5)、空穴传输层(6)、发光层(7)、电子传输层(8)和阴极(4)的有机发光器件的实例。在这样的结构中,由化学式1表示的化合物可包含在空穴注入层、空穴传输层、发光层和电子传输层中的一个或更多个层中。
根据本公开内容的有机发光器件可通过使用本领域已知的材料和方法来制备,不同之处在于一个或更多个有机材料层包含由化学式1表示的化合物。此外,在有机发光器件包括多个有机材料层的情况下,有机材料层可由相同材料或不同材料形成。
例如,根据本公开内容的有机发光器件可通过在基底上依次层合第一电极、有机材料层和第二电极来制备。在这种情况下,有机发光器件可通过如下过程来制备:通过使用PVD(物理气相沉积)法(例如溅射法或电子束蒸发方法)在基底上沉积金属或具有导电性的金属氧化物或其合金以形成阳极,在其上形成包括空穴注入层、空穴传输层、发光层和电子传输层的有机材料层,然后在其上沉积可以用作阴极的材料。除这样的方法之外,有机发光器件可通过在基底上依次沉积阴极材料、有机材料层和阳极材料来制备。
此外,在生产有机发光器件期间,由化学式1表示的化合物可通过真空沉积法以及溶液涂覆法形成为有机材料层。在此,溶液涂覆法意指旋涂、浸涂、刮涂、喷墨印刷、丝网印刷、喷涂法、辊涂等,但不限于此。
除这样的方法之外,有机发光器件可通过在基底上依次沉积阴极材料、有机材料层和阳极材料来制备(国际公开WO 2003/012890)。然而,制备方法不限于此。
在一个实例中,第一电极为阳极,第二电极为阴极,或者第一电极为阴极,第二电极为阳极。
作为阳极材料,通常优选使用具有大功函数的材料,以使空穴可以顺利地注入有机材料层。阳极材料的具体实例包括:金属,例如钒、铬、铜、锌和金,或其合金;金属氧化物,例如锌氧化物、铟氧化物、铟锡氧化物(ITO)和铟锌氧化物(IZO);金属和氧化物的组合,例如ZnO:Al或SnO2:Sb;导电聚合物,例如聚(3-甲基噻吩)、聚[3,4-(亚乙基-1,2-二氧基)噻吩](PEDOT)、聚吡咯和聚苯胺;等等,但不限于此。
作为阴极材料,通常优选使用具有小功函数的材料,以使电子可以容易注入有机材料层。阴极材料的具体实例包括:金属,例如镁、钙、钠、钾、钛、铟、钇、锂、钆、铝、银、锡和铅,或其合金;多层结构材料,例如LiF/Al或LiO2/Al;等等,但不限于此。
空穴注入层是注入来自电极的空穴的层,并且空穴注入材料优选为这样的化合物:其具有传输空穴的能力,对阳极中具有空穴注入效应,对发光层或发光材料具有优异的空穴注入效应,防止发光层中产生的激子迁移至电子注入层或电子注入材料,并且具有优异的薄膜形成能力。空穴注入材料的HOMO(最高占据分子轨道)优选在阳极材料的功函数与周围有机材料层的HOMO之间。空穴注入材料的具体实例包括金属卟啉、低聚噻吩、基于芳基胺的有机材料、基于六腈六氮杂苯并菲的有机材料、基于喹吖啶酮的有机材料、基于苝的有机材料、蒽醌、基于聚苯胺和聚噻吩的导电聚合物等,但不限于此。
空穴传输层是接收来自空穴注入层的空穴并将空穴传输至发光层的层,并且空穴传输材料为可以接收来自阳极或空穴注入层的空穴并将空穴传输至发光层的材料,并且对空穴具有大的迁移率的材料是合适的。其具体实例包括基于芳基胺的有机材料、导电聚合物、同时存在共轭部分和非共轭部分的嵌段共聚物等,但不限于此。
发光材料为可以接收分别来自空穴传输层和电子传输层的空穴和电子并使空穴和电子结合而在可见光区域发光的材料。发光材料优选为对荧光或磷光具有良好量子效率的材料。其具体实例包括8-羟基-喹啉铝配合物(Alq3);基于咔唑的化合物;二聚苯乙烯基化合物;BAlq;10-羟基苯并喹啉-金属化合物;基于苯并唑、苯并噻唑和苯并咪唑的化合物;基于聚(对亚苯基亚乙烯)(PPV)的聚合物;螺环化合物;聚芴;红荧烯等,但不限于此。
发光层可包含主体材料和掺杂剂材料。主体材料的实例包括缩合芳族环衍生物、含杂环化合物等。缩合芳族环衍生物的具体实例包括蒽衍生物、芘衍生物、萘衍生物、并五苯衍生物、菲化合物、荧蒽化合物等,含杂环化合物的具体实例包括咔唑衍生物、二苯并呋喃衍生物、梯型呋喃化合物、嘧啶衍生物等,但材料不限于此。
掺杂剂材料的实例包括芳族胺衍生物、苯乙烯胺化合物、硼配合物、荧蒽化合物、金属配合物等。具体地,芳族胺衍生物为具有经取代或未经取代的芳基氨基的缩合芳族环衍生物,其实例包括具有芳基氨基的芘、蒽、和二茚并芘等,苯乙烯胺化合物是其中经取代或未经取代的芳基胺中取代有至少一个芳基乙烯基的化合物,其中选自芳基、甲硅烷基、烷基、环烷基和芳基氨基中的一个或两个或更多个取代基是经取代或未经取代的。其具体实例包括苯乙烯胺、苯乙烯二胺、苯乙烯三胺、苯乙烯四胺等,但不限于此。此外,金属配合物的实例包括铱配合物、铂配合物等,但不限于此。
电子传输材料是接收来自电子注入层的电子并将电子传输至发光层的层。对于电子传输材料,可以良好地接收来自阴极的电子并将电子传输至发光层且对电子具有大的迁移率的材料是合适的。其具体实例包括8-羟基喹啉的Al配合物;包含Alq3的配合物;有机自由基化合物;羟基黄酮-金属配合物等,但不限于此。电子传输层可以与如根据现有技术使用的预先期望阴极材料一起使用。特别地,合适的阴极材料的实例为具有小功函数的常见材料,后接铝层或银层。其具体实例包括铯、钡、钙、镱和钐,并且每种情况都后接铝层或银层。
电子注入层是注入来自电极的电子的层,并且优选为这样的化合物:其具有传输电子的能力,具有从阴极注入电子的效应,并且对发光层或发光材料具有优异的电子注入效应,防止发光层中产生的激子迁移到空穴注入层,并且具有优异的薄膜形成能力。其具体实例包括芴酮、蒽醌二甲烷、联苯醌、噻喃二氧化物、唑、二唑、三唑、咪唑、苝四羧酸、亚芴基甲烷、蒽酮等,及其衍生物,金属配合物化合物,含氮五元环衍生物等,但不限于此。
金属配合物化合物的实例包括8-羟基喹啉锂、双(8-羟基喹啉)锌、双(8-羟基喹啉)铜、双(8-羟基喹啉)锰、三(8-羟基喹啉)铝、三(2-甲基-8-羟基喹啉)铝、三(8-羟基喹啉)镓、双(10-羟基苯并[h]喹啉)铍、双(10-羟基苯并[h]喹啉)锌、双(2-甲基-8-喹啉)氯镓、双(2-甲基-8-喹啉)(邻甲酚)镓、双(2-甲基-8-喹啉)(1-萘酚)铝、双(2-甲基-8-喹啉)(2-萘酚)镓等,但不限于此。
根据所使用的材料,根据本公开内容的有机发光器件可为前侧发光型、后侧发光型或双侧发光型。
此外,除有机发光器件之外,由化学式1表示的化合物可包含在有机太阳能电池或有机晶体管中。
在以下实施例中,将详细描述由化学式1表示的化合物和包含其的有机发光器件的制备。然而,这些实施例仅为了举例说明的目的而提出,并且本发明的范围不限于此。
制备例1:化合物A2的制备
1)化合物A1的制备
使3-溴-5-氯苄腈(30g,139mmol)和(3-氰基苯基)硼酸(22g,152mmol)溶解在300ml四氢呋喃,向其中添加碳酸钠(Na2CO3)的2M溶液(210mL)和四(三苯基膦)钯(0)(2g,1mmol%),并回流12小时。在反应完成之后,将混合物冷却至室温,并用水和甲苯对所得混合物进行萃取3次。分离甲苯层,用硫酸镁干燥,并在减压下蒸馏滤液。使用氯仿和乙醇使所得混合物重结晶三次以制备化合物A1(20g,产率61%;MS:[M+H]+=239)。
2)化合物A2的制备
将化合物A1(20g,84mmol)、双(频哪醇)二硼(23g,92mmol)、乙酸钾(25g,251mmol)、二亚苄基丙酮钯(1.4g,2.5mmol)和三环己基膦(1.4g,5.0mmol)添加到二烷(300mL)中,并回流12小时。在反应完成之后,将反应混合物冷却至室温,并在减压下蒸馏以除去溶剂。然后使其溶解在氯仿中,并用水洗涤3次。分离有机层并用硫酸镁干燥。然后在减压下对其进行蒸馏以制备化合物A2(22g,产率78%;MS:[M+H]+=331)。
制备例2:化合物B2的制备
1)化合物B1的制备
以与化合物A1的制备例1中相同的方式制备化合物B1(28g,产率70%;MS:[M+H]+=291),不同之处在于使用(4-(吡啶-2-基)苯基)硼酸(30g,152mmol)代替(3-氰基苯基)硼酸(22g,152mmol)。
2)化合物B2的制备
以与化合物A2的制备例1中相同的方式制备化合物B2(20g,产率70%;MS:[M+H]+=382),不同之处在于使用化合物B1(20g,69mmol)代替化合物A1。
制备例3:化合物C2的制备
1)化合物C1的制备
以与化合物A1的制备例1中相同的方式制备化合物C1(32g,产率61%;MS:[M+H]+=379),不同之处在于使用(4-(9H-咔唑-9-基)苯基)硼酸(44g,152mmol)代替(3-氰基苯基)硼酸(22g,152mmol)。
2)化合物C2的制备
以与化合物A2的制备例1中相同的方式制备化合物C2(20g,产率81%;MS:[M+H]+=471),不同之处在于使用化合物C1(20g,53mmol)代替化合物A1。
制备例4:化合物D2的制备
1)化合物D1的制备
以与化合物A1的制备例1中相同的方式制备化合物D1(27g,产率65%;MS:[M+H]+=304),不同之处在于使用二苯并[b,d]呋喃-4-基硼酸(32g,152mmol)代替(3-氰基苯基)硼酸(22g,152mmol)。
2)化合物D2的制备
以与化合物A2的制备例1中相同的方式制备化合物D2(20g,产率81%;MS:[M+H]+=471),不同之处在于使用化合物D1(20g,53mmol)代替化合物A1。
制备例5:化合物E2的制备
1)化合物E1的制备
以与化合物A1的制备例1中相同的方式制备化合物E1(35g,产率80%;MS:[M+H]+=320),不同之处在于使用二苯并[b,d]噻吩-4-基硼酸(35g,152mmol)代替(3-氰基苯基)硼酸(22g,152mmol)。
2)化合物E2的制备
以与化合物A2的制备例1中相同的方式制备化合物E2(20g,产率78%;MS:[M+H]+=411),不同之处在于使用化合物E1(20g,53mmol)代替化合物A1。
制备例6:化合物F2的制备
1)化合物F1的制备
以与化合物A1的制备例1中相同的方式制备化合物F1(39g,产率77%;MS:[M+H]+=364),不同之处在于使用三亚苯-2-基硼酸(42g,152mmol)代替(3-氰基苯基)硼酸(22g,152mmol)。
2)化合物F2的制备
以与化合物A2的制备例1中相同的方式制备化合物F2(20g,产率79%;MS:[M+H]+=456),不同之处在于使用化合物F1(20g,55mmol)代替化合物A1。
制备例7:化合物G2的制备
1)化合物G1的制备
以与化合物A1的制备例1中相同的方式制备化合物G1(30g,产率70%;MS:[M+H]+=314),不同之处在于使用菲-9-基硼酸(34g,152mmol)代替(3-氰基苯基)硼酸(22g,152mmol)。
2)化合物G2的制备
以与化合物A2的制备例1中相同的方式制备化合物G2(17g,产率65%;MS:[M+H]+=406),不同之处在于使用化合物G1(20g,55mmol)代替化合物A1。
制备例8:化合物sub 1的制备
1)化合物sub 1-1的制备
将化合物R3(50g,114mmol)、4-溴萘-1-醇(21g,114mmol)添加到300mL四氢呋喃中,搅拌混合物并回流。使碳酸钾(48g,345mmol)溶解在100mL水中,然后将其添加到混合物中。在充分搅拌混合物之后,向其中添加四三苯基-膦钯(4g,3mmol)。在反应12小时之后,将温度冷却至室温,并过滤。用氯仿和水对滤液进行萃取,然后用硫酸镁干燥有机层。然后在减压下对有机层进行蒸馏并使用乙醇使其重结晶。将所得固体过滤并干燥以制备化合物sub 1-1(41g,产率80%,MS:[M+H]+=452)。
2)化合物sub 1的制备
将化合物sub 1-1(30g,66mmol)添加到300mL乙腈中,并搅拌。将碳酸钾(18g,133mmol)与50mL水混合并添加到其中。然后,在用水浴加热的同时缓慢添加1-丁烷磺酰氟(15g,100mmol)。在反应约1小时之后,使反应终止。在将温度冷却至室温之后,分离水层和有机层,并在减压下对有机层进行蒸馏以制备化合物sub 1(34g,产率90%,MS:[M+H]+=584)。
制备例9:化合物sub 2的制备
1)化合物sub 2-1的制备
以与化合物sub 1-1的制备例8中相同的方式制备化合物sub 2-1(39g,产率75%;MS:[M+H]+=452),不同之处在于使用7-溴萘-2-醇(34g,152mmol)代替4-溴萘-1-醇(22g,152mmol)。
2)化合物sub 2的制备
以与化合物sub 1的制备例8中相同的方式制备化合物sub 2(36g,产率92%;MS:[M+H]+=584),不同之处在于使用化合物sub 2-1(30g,66mmol)代替化合物sub 1-1(30g,66mmol)。
制备例10:化合物sub 3的制备
1)化合物sub 3-1的制备
以与化合物sub 1-1的制备例8中相同的方式制备化合物sub 3-1(31g,产率61%;MS:[M+H]+=452),不同之处在于使用1-溴萘-2-醇(34g,152mmol)代替4-溴萘-1-醇(22g,152mmol)。
2)化合物sub 3的制备
以与化合物sub 1的制备例8中相同的方式制备化合物sub 3(34g,产率88%;MS:[M+H]+=584),不同之处在于使用化合物sub 3-1(30g,66mmol)代替化合物sub 1-1(30g,66mmol)。
制备例11:化合物sub 4的制备
1)化合物sub 4-1的制备
以与化合物sub 1-1的制备例8中相同的方式制备化合物sub 4-1(38g,产率73%;MS:[M+H]+=452),不同之处在于使用6-溴萘-2-醇(34g,152mmol)代替4-溴萘-1-醇(22g,152mmol)。
2)化合物sub 4的制备
以与化合物sub 1的制备例8中相同的方式制备化合物sub 4(34g,产率88%;MS:[M+H]+=584),不同之处在于使用化合物sub 4-1(30g,66mmol)代替化合物sub 1-1(30g,66mmol)。
制备例12:化合物sub 5的制备
将化合物R4(30g,69mmol)、1-溴-3-碘苯(20g,69mmol)添加到300mL四氢呋喃中,搅拌混合物并回流。使碳酸钾(29g,206mmol)溶解在90mL水中,然后将其添加到混合物中。在充分搅拌混合物之后,向其中添加四三苯基-膦钯(2g,2mmol)。在反应12小时之后,将温度冷却至室温,并过滤。用氯仿和水对滤液进行萃取,然后用硫酸镁干燥有机层。然后在减压下对有机层进行蒸馏并使用乙醇使其重结晶。将所得固体过滤并干燥以制备化合物sub5(20g,产率63%,MS:[M+H]+=464)。
实施例1:化合物1的制备
在使化合物R1(20g,51mmol)和化合物A2(17g,51mmol)分散在四氢呋喃(150mL)中之后,向其中添加2M碳酸钾水溶液(K2CO3水溶液)(77mL),然后向其中添加四三苯基膦钯[Pd(PPh3)4](1g,1mol%),接着搅拌并回流12小时。将温度冷却至室温并过滤所得固体。使用四氢呋喃和乙酸乙酯使滤出的固体重结晶,过滤然后干燥以制备化合物1(15g,产率60%;MS:[M+H]+=512)。
实施例2:化合物2的制备
以与化合物1的实施例1中相同的方式制备化合物2(14g,产率55%;MS:[M+H]+=512),不同之处在于使用化合物R2(20g,51mmol)代替化合物R1。
实施例3:化合物3的制备
以与化合物1的实施例1中相同的方式制备化合物3(20g,产率61%;MS:[M+H]+=638),不同之处在于使用化合物sub 1(30g,51mmol)代替化合物R1。
实施例4:化合物4的制备
以与化合物1的实施例1中相同的方式制备化合物4(23g,产率71%;MS:[M+H]+=638),不同之处在于使用化合物sub 2(30g,51mmol)代替化合物R1。
实施例5:化合物5的制备
以与化合物1的实施例1中相同的方式制备化合物5(15g,产率48%;MS:[M+H]+=638),不同之处在于使用化合物sub 3(30g,51mmol)代替化合物R1。
实施例6:化合物6的制备
以与化合物1的实施例1中相同的方式制备化合物6(25g,产率75%;MS:[M+H]+=638),不同之处在于使用化合物sub 4(30g,51mmol)代替化合物R1。
实施例7:化合物7的制备
以与化合物1的实施例1中相同的方式制备化合物7(11g,产率39%;MS:[M+H]+=588),不同之处在于使用化合物sub 5(24g,51mmol)代替化合物R1。
实施例8:化合物8的制备
在使化合物R2(20g,51mmol)和化合物B2(20g,51mmol)分散在四氢呋喃(150mL)中之后,向其中添加2M碳酸钾水溶液(K2CO3水溶液)(77mL),然后向其中添加四三苯基膦钯[Pd(PPh3)4](1g,1mol%),接着搅拌并回流12小时。将温度冷却至室温并过滤所得固体。使用四氢呋喃和乙酸乙酯使滤出的固体重结晶,过滤然后干燥以制备化合物8(13g,产率42%;MS:[M+H]+=588)。
实施例9:化合物9的制备
以与化合物8的实施例8中相同的方式制备化合物9(18g,产率55%;MS:[M+H]+=652),不同之处在于使用化合物C2(24g,51mmol)代替化合物B2。
实施例10:化合物10的制备
以与化合物8的实施例8中相同的方式制备化合物10(18g,产率63%;MS:[M+H]+=577),不同之处在于使用化合物D2(20g,51mmol)代替化合物B2。
实施例11:化合物11的制备
以与化合物8的实施例8中相同的方式制备化合物11(18g,产率60%;MS:[M+H]+=592),不同之处在于使用化合物E2(20g,51mmol)代替化合物B2。
实施例12:化合物12的制备
以与化合物8的实施例8中相同的方式制备化合物12(23g,产率71%;MS:[M+H]+=636),不同之处在于使用化合物F2(24g,51mmol)代替化合物B2。
实施例13:化合物13的制备
以与化合物8的实施例8中相同的方式制备化合物13(19g,产率64%;MS:[M+H]+=587),不同之处在于使用化合物G2(21g,51mmol)代替化合物B2。
实施例14:化合物14的制备
在使化合物R5(18g,51mmol)和化合物G2(21g,51mmol)分散在四氢呋喃(150mL)中之后,向其中添加2M碳酸钾水溶液(K2CO3水溶液)(77mL),然后向其中添加四三苯基膦钯[Pd(PPh3)4](1g,1mol%),接着搅拌并回流12小时。将温度冷却至室温并过滤所得固体。使用四氢呋喃和乙酸乙酯使滤出的固体重结晶,过滤然后干燥以制备化合物14(11g,产率39%;MS:[M+H]+=587)。
实施例15:化合物15的制备
以与化合物14的实施例14中相同的方式制备化合物15(25g,产率73%;MS:[M+H]+=663),不同之处在于使用化合物R6(20g,51mmol)代替化合物R5。
实施例16:化合物16的制备
以与化合物14的实施例14中相同的方式制备化合物16(16g,产率57%;MS:[M+H]+=534),不同之处在于使用化合物R7(13g,51mmol)代替化合物R5。
实施例17:化合物17的制备
以与化合物14的实施例14中相同的方式制备化合物17(18g,产率62%;MS:[M+H]+=560),不同之处在于使用化合物R8(15g,51mmol)代替化合物R5。
实验例1
将其上施加有厚度为的ITO(氧化铟锡)薄膜的玻璃基底(corning 7059玻璃)放入其中溶解有清洁剂的蒸馏水中,并通过超声波进行洗涤。所使用的清洁剂为商购自Fischer Co.的产品,并且蒸馏水为通过使用商购自Millipore Co.的过滤器过滤两次的蒸馏水。在将ITO洗涤30分钟之后,通过使用蒸馏水重复进行两次超声波洗涤10分钟。在用蒸馏水洗涤完成之后,按照异丙醇、丙酮和甲醇溶剂的顺序进行超声波洗涤,并进行干燥。
在上述制备的ITO透明电极上,在真空下以的厚度使以下化合物HI-1热沉积以形成空穴注入层。在空穴注入层上,在真空下以的厚度使以下化合物HT-1沉积以形成空穴传输层,并在真空下使主体H1和掺杂剂化合物D1(2.5重量%)沉积为厚度为的发光层。在发光层上,在真空下以的厚度使以下化合物ET-A沉积以形成a-电子传输层。在a-电子传输层上,在真空下使实施例1中制备的化合物1和LiQ(喹啉锂)以1:1的重量比沉积以形成厚度为的电子注入和传输层。在电子注入和传输层上分别以和的厚度依次沉积氟化锂(LiF)和铝以形成阴极。
在上述过程中,保持有机材料的气相沉积速率为/秒至/秒,保持阴极的氟化锂的沉积速率为/秒,保持铝的沉积速率为/秒,以及保持气相沉积期间的真空度为2×10-7托至5×10-6托来制造有机发光器件。
实验例2至17
以与实验例1中相同的方式制备有机发光器件,不同之处在于使用下表1中描述的化合物代替化合物1。
比较实验例1至3
以与实验例1中相同的方式制备有机发光器件,不同之处在于使用下表1中描述的化合物代替化合物1。在下表1中,化合物A、化合物B和化合物C如下:
通过向实验例和比较实验例中制备的有机发光器件施加电流来测量驱动电压、效率、色坐标和寿命,结果示于下表1中。寿命(LT95)限定为当将初始亮度视作100%时亮度降低至95%所需要的时间,并在50mA/cm2的电流密度下进行测量。
[表1]
如表1所示,确定与使用比较例1至3的化合物的情况相比,当使用本公开内容的化合物作为电子传输层材料时,表现出优异的稳定性。
[附图标记]
1:基底
2:阳极
3:发光层
4:阴极
5:空穴注入层
6:空穴传输层
Claims (10)
1.一种由以下化学式1表示的化合物:
[化学式1]
在化学式1中,
L1和L2各自独立地为单键;经取代或未经取代的C6-60亚芳基;或者经取代或未经取代的包含O、N、Si和S中至少一者的C2-60亚杂芳基,
Ar1为包含选自N、O和S中的1至3个杂原子的C2-60杂芳基,
Ar2为选自以下结构式中的任一者,
X为N(R'1)、C(R'2)(R'3)、Si(R'4)(R'5)、S或O,以及
R'1至R'7和R1至R19各自独立地为氢;氘;卤素;氰基;硝基;胺基;经取代或未经取代的C1-60烷基;C1-60卤代烷基;C1-60卤代烷氧基;经取代或未经取代的C3-60环烷基;经取代或未经取代的C2-60烯基;经取代或未经取代的C6-60芳基;或者经取代或未经取代的包含O、N、Si和S中至少一者的C2-60杂环基。
2.根据权利要求1所述的化合物,
其中L1为单键或选自以下结构式中的任一者:
3.根据权利要求1所述的化合物,
其中L2为单键、
4.根据权利要求1所述的化合物,
其中Ar1为选自以下结构式中的任一者,
Y1至Y3中的两者为N,另一者为CH,
Z为N(Ar7)、S或O,以及
Ar3至Ar7为经取代或未经取代的C6-60芳基。
5.根据权利要求4所述的化合物,
其中Ar3至Ar7为苯基或联苯基。
6.根据权利要求1所述的化合物,
其中Ar1为选自以下结构式中的任一者:
7.根据权利要求1所述的化合物,
其中R1为氰基、三氟甲基或三氟甲氧基。
8.根据权利要求1所述的化合物,
其中R2至R19为氢。
9.根据权利要求1所述的化合物,
其中所述化合物选自以下化合物:
10.一种有机发光器件,包括:第一电极;设置成面向所述第一电极的第二电极;以及设置在所述第一电极与所述第二电极之间的一个或更多个有机材料层,其中所述有机材料层的一个或更多个包含根据权利要求1至9中任一项所述的化合物。
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